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LONDON, ENGLAND - JUNE 06: Simon Cowell (L) and Jackie St Clair pose in the press room at the Philips British Academy Television Awards (BAFTA) at London Palladium on June 6, 2010 in London, England. (Photo by Jon Furniss/WireImage) *** Local Caption *** Simon Cowell;Jackie St Clair

Simon Cowell's Romance Timeline

The latest earthquake in the Simon Cowell romantic soap opera came this week with the news that the 53-year-old is reportedly going to become a first-time dad along with Lauren Silverman, the soon-to-be-divorced wife of his mogul friend Andrew.

Since the recording industry executive first broke into the public eye in the U.K. as a judge on Britain's "Pop Idol," Cowell's romantic life has been filled with colorful figures, on-again/off-again engagements, and several celebrity liaisons. In the words of one of those colorful exes, Sinitta, "Sex is so important to Simon. That's his trouble. It clouds his judgment."

Check out some of the major stops along Simon Cowell's rocky romantic road.